


Day 3 (First Time)

by orphan_account



Series: Widogast 30 Day Nsfw Challenge [3]
Category: Critical Role (Web Series)
Genre: 30 Day OTP Porn Challenge, Anal Fingering, Anal Sex, Established Relationship, First Time, M/M, Plot What Plot/Porn Without Plot
Language: English
Status: Completed
Published: 2018-06-21
Updated: 2018-06-21
Packaged: 2019-05-26 09:56:08
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,975
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/14998358
Author URL: https://archiveofourown.org/users/orphan_account/pseuds/orphan_account
Summary: Around the campfire Jester asks the couples in the group about their first times, which makes Mollymauk recall his and Caleb's first





	Day 3 (First Time)

**Author's Note:**

> Attempting to do the 30 day nsfw otp challenge with the ship that slowly becoming my new favorite. It's been while since I've written, so its just trying to get me back into the swing of things again. Sorry if I'm a bit rusty especially with writing new characters. If you like it feel free to kudo, comment, or send encouragement

     The fire residing in the middle of their camp site roars strongly, the occasional snap, and flare of smoke keeping the group of weary travelers warm and comfortable. There is a strong smell of cured meats, as Yasha beings to carve up the large piece of fresh beast, dividing up more than enough for each member of the group. A butcher had given it to them as they made their way out of town yesterday, as an offering for saving his family, which will be able to feed the group for a few days. Nott's endless flask is being passed around the group, each person taking a swig or so, before passing it along, all of them are in a good mood. Fully rested from the night before, money in their pockets, and well stocked for the days of travel they had ahead of him.

     Caleb and Mollymauk are leaning up against each other, Caleb's eyes trained on the fire, as Molly makes quiet conversation with the rest of people presiding around the fire. Nott sits unfazed on the dirt ground, fiddling with her crossbow, and going through the small collection of trinkets she'd stolen recently. Beauregard is not so subtlety checking out Yasha, as her arms flex with each cut she makes with the large knife into the pig. Frumpkin sits next to Yasha attempting to steal some meat, as it's being carved up, Yasha seems to accidentally drop a piece of fat next to the cat, who munches it up happily. Jester is sitting on her cloak, reading through her copy of Tusk Love for the umpteenth time, occupied for now, but on the edge of boredom. Fjord is a few yards away, pacing the edge of camp, looking out for anything suspicious.

     "C'mon Fjord, there's nothing out there, come get something to eat." Yasha calls out, passing around the pork she had carved up, meat filling up various bowls, with some left over roasted potatoes and carrots on the side. Jester puts her book on her coat, both beginning to show wear and tear through travels, taking the warm bowl in her hands. Fjord comes back from his watch putting his falchion back in it's sheath, taking the bowl Yasha hands to him, and sitting down between Beau and Jester. As Nott gets her bowl, the crossbow clatters out of her hands where she was repairing it, making a bolt wizz out into the dark woods around them, making a flurry of birds fly away from where it landed. The group putting their food down, all reaching for their weapons, and immediately on edge. "Sorry, sorry, sorry!" Nott squeaks out right away with her hands tossed in the air, "My bad. Apologizes." The group's tension dissipates as the weapons are returned, and they all go back to their dinner after a moments pause.

     "Beau you got a little something," Fjord points to Beau, who slides the back of her hand over her mouth. "Ah, man. Did I...did I get it? How bad is it?" Beaurguard asks, wondering how much of a mess she had made. "Not quiet what I was referring to actually," Fjord says a bit awkwardly, pointing more towards the bruise on her shoulder he had noticed wondering how it must have happened, considering it had been a few days since the last battle. Yasha peaks around Beau checking out the mark as well, with a smirk the barbarian leans back and goes back to her food. "It's nothing, don't even worry about. Just a little bruise is all, you know?" Beau tries to brush it off, pulling her cloak up to cover the mark back up again. The rest of them are curious, but seem to let it go, well all of them except Jester. "Is that a hickey Beau?" She asks cheerfully, putting her food to the side, seemingly more interested.

     "Uh, yeah. Yeah it is. It's no big deal you know. Just a little mark. Don't even worry about it." Beau knows shes fucked, since Jester is now interested, and more than likely won't stop until she has all the information she can pull. "Well, someone had a good time last night." Jester says with a smile, no longer looking at Beauregard, but now at Yasha who is unfazed by this conversation. "C'mon Jester, it's no big deal. It just a little love bite." Beau tries again to drop the conversation, but Caleb cuts in before Jester can. "Ah, no. I think this is fair. I mean anytime me or Mollymauk have any sort of, mark we get teased about it for days. About time it is someone else." Pleased with what Caleb has said, Mollymauk wraps an arm around Caleb a little tighter. "I agree. I mean, when we started dating, there was endless questioning. With you two though, there has been hardly any sort of snide comments." Mollymauk notes.

     "Yeah, because they're scary." Nott immediately explains, not meaning any ill will, but just a general acknowledgment. Which was true, both of the girls where quite muscular, and with Yasha being the tallest and strongest of the group. "We can be scary too, you know. I mean Mollymauk can be quiet intimidating." Caleb tries to defend himself and Mollymauk for some reason, who didn't quiet care really about the teasing typically. Molly rolls his eyes, going back to his dinner, letting this play out on it own. Jester gives Caleb a sympathetic look, basically saying she didn't believe any of that, glancing back to Beau and Yasha. "Was it any good though?" Jester asks without filter to Beau, who opens her mouth wide at a loss for words, Fjord coughing a bit on what was in his mouth. Yasha seems to be also waiting for Beauregard to answer as well.

     Flushed with a bit of pink to her face, Beau stumbles over her words before answer, "It was, really good. Great actually. Yeah." She manages out, taking a huge swig out of Nott's flask, and swallowing it down with a grimace. Yasha shrugs in response not wanting to add anymore entertainment. Jester seemingly satisfied for now, lets Beauregard back to her dinner, "Alright, if you say so, that wasn't very detailed," she huffs out glancing back at Caleb and Mollymauk. "What about you two? What was your first time like?" The blue tiefling asks, hoping to get something juicy out of someone. "And I am done. I want nothing to do with this." Caleb announced, bowl put on the ground and heading into their tent, social anxiety getting to the best of him once again. Mollymauk watches Caleb leave, figuring he was probably fine until later tonight, and goes back to Jester's waiting face. "Well, it was interesting..." Molly started, thinking back to his and Caleb's first time, that had happened really not too long ago it felt like.

-

     Mollymauk and Caleb had been flirting around this happening for a while, being with each other as much as they do, sharing a tent when they camp for the night, and stealing little moments when they could if the group was otherwise occupied. All they could do was steal kisses, some wandering hands, and close cuddling was all they had managed so far. To afraid to make noise in the night where the Mighty Nien decide to camp out for the evening, or have the group aware of their relationship. They weren't uncomfortable sharing that they were together, just wanting to take things slowly for the moment.

     Having been in the circus Mollymauk is very knowledgeable in relationships on the road, it doesn't always end the best ways, tensions run high due to months on the road, poor sleep, not always enough food. It was difficult to be positive in relationships, and most travelers preferred one time things, as they passed through town. It being a general rule that flings in groups usually ended in bad drama. Mollymauk had seen plenty of fights and members leave the circus for relationships blowing up in flames. The last thing Caleb and Molly wanted to do was compromise the group, causing any sort of disband, because of them.

     They still had needs though, and for the first time they had a inn room to themselves for the whole night, since that night on watch where they had confessed their feelings to each other and kissed for the first time. Mollymauk was bit excited about the concept of spending the night together, first going through his ritual of folding his scimitars in his coat, resting them securely on the table in the room as well as taking his boots off. Caleb is perched on the bed, eyes locked the pages of the new book he procured in the bookshop he discovered upon entering town. A powerful spell book that through some convincing Caleb got for a steal, well Nott payed for it, either way it was a good deal and Caleb was happy. Happy, but distracted from Mollymauk, which wasn't going to do.

     Sitting down behind Caleb, Mollymauk wraps his arms around the ginger's shoulders, placing a kiss right below his left ear. Blinking a bit and coming back to his senses, Caleb perks up turning his head slightly, as if to see who was there. "Hey," Molly, says with a toothy smile. "Hello." Caleb replied softly, not quiet closing his book, but interest was peaked enough for Molly's liking. "So, we have a room with a bed, an entire evening together, with nothing to worry about. You wanna spend it reading your book?" Molly purred, tail twitching behind him, reaching up and flicking Caleb's ear. Waving the tail off, Caleb memorizes the page he left on, before putting the hard leather book to the side. "What did you uh, have in mind?" Caleb attempted to say something more smooth and coy like, but it was the best he could come up with.

     "Um, anything with you sounds wonderful." Mollymauk was already flustered, stuff like this never bothered him before, he wasn't a virgin by any means and was one to peruse paying for evening company. It was just different with Caleb, because this meant something, and he didn't want to mess their first time up. He still really wanted to have sex with Caleb though, like a lot. "I have a few ideas though." Molly's tail sways back from where Caleb knocked it away, and curls it under Caleb's undershirt. There isn't a lot of feeling in Molly's tail to really be sure he made it through, but Caleb squirms and nudges Molly back to fall on the bed, enough to know Caleb got the message. Molly watches from the bed as Caleb gets up, shucking his long coat off, toeing his boots off into the corner. Caleb's slightly less dirty shirt follows, revealing the long thin chest covered in pale skin, and dusting of ginger body hair.

     Mollymauk getting where this was heading, works his loose cream shirt off, and pulls it over his head. While, attempts to anyways, he manages to somehow get the loose cloth caught up in his horns, which he could normally deal with, but the jewelry gets caught up it it as well. Mollymauk groans, as he feels the bed dip, and Caleb's nimble fingers unhook the chains and dangles out of the caught threads. "Where would you be without me Mr. Tealeaf?" Caleb asks as he tosses the shirt to the side, admiring the large peacock and snake tattoo in their entirety, now that the shirt was free. "Probably in shackles or maybe another circus full of reanimated corpses again. Possibly both, depending on the act." Molly tries his best to recover smoothly, but honestly with a half naked Caleb practically in his lap, he no longer really cares.

     Caleb leans down and kisses Mollymauk, kissing the tiefling could handle, they'd done it plenty of times before. It starts off slow a simple long pecks here and there, occasional gentle touching, as they both got comfortable on the small bed. The kissing deepens then, both of them having more access to touch each other, their legs entangled in desperate need to be closer. Caleb caressing Molly's back which is sensitive in spots, making Mollymauk moan if Caleb's fingers massaged deep enough in the right spot. Molly went the more direct route, teasing Caleb's hips and sides, before simply palming the growing tent in Caleb's pants the longer they touched and kissed. Both of them relatively quiet, besides the soft moan and smalls gaps for air, while they kissed.

     Molly suddenly remembers how far this evening could go, when Caleb's wandering hand on his back, slips into his pants and past his tail. "This okay?" Caleb pulls away from the kiss to catch his breath and asks before daring to go any further, it's not the first time they have done intimate things with each other, but this one was a first. "Yeah, yeah. Keep going." Molly wasn't about to complain or stop this by any means, when it comes to sex Molly rarely cares what position he's in, as long as he's apart of it. He didn't assume Caleb was a bottom, but he did think there might have been a conversation on preference beforehand. Caleb's fingers press against his entrance, as Molly tries his best to relax his body, he doubts they had lube on hand, but they could manage hopefully.

     Caleb seems to be taking his time at least longer than Molly would like him to, so he glances up seeing if maybe Caleb hadn't heard him properly. Instead he sees Caleb's mouth moving, muttering something under his breath, before stopping. This time when Caleb's fingers pressed against Molly's entrance they were wet and the first digit slips in with ease. Mollymauk groans, burring his head in Caleb's shoulder, getting used to the intrusion slowly. It's been a while since he's done this apparently. "You doing okay?" Caleb asks, and Molly can hear how deeply concerned Caleb is, just in the tone he's using. Mollymauk looks up, his red eyes a shade darker than usual, "Yeah, just...what was that?" His partner looks at Molly slightly confused and wiggles the finger that's deep inside the tiefling. Mollymauk bites down hard on his lip and bucks his hips not expecting that, before regaining himself to glare up at Caleb. "I meant the spell." Sure Molly loved magic, but he was a bit concerned what could be the aftermath of whatever arcane thing was happening.

     "Oh, it's a loosening spell of some sort. I taught it to Nott, so she could dismantle traps and open locks, if the situation required it." Caleb continued his ministrations, using the finger inside Molly's ass to carefully open him up as gently as he could. "It's perfectly safe, and I only casted it on my hand. You don't need to worry." Mollymauk pressed himself against Caleb as soon as the fingering in his ass had started again, the mix of pressure, pleasure and the smallest bit of pain, being too much for his mind to handle. If he tried to talk, he's sure all Caleb would get was whimpers and moans. The movement does stop for a moment as the finger slips out, Molly lifts his head up, using that moment to say what he wanted to earlier. "I'm glad I won't wake up tomorrow with some weird symptoms, because of whatever that spell was, but also I'm gonna say that we don't mention Nott while in bed. Or any of our friends really. I mean, she practically your mother, right?"

     The wizard shrugs seeming to agree with that statement, and finishes stretching his hand out, from where it was starting to cramp up. "Alright, I can agree with that. Do you mind taking these off, so I can do this a little easier?" Caleb asks as his thumb dips and tugs at the hem of Mollymauk's pants. "Only, if you take yours off as well, Mister Caleb." But not needing to be told twice, or waiting for an response back, Molly undoes the buttons and tugs his pants down his legs making his tail and almost painfully hard cock spring free. The tip of it a dark purple, and it makes Molly realize how much he wants to come right now. Caleb seemed to have the plan to fuck him tonight though, so maybe it was better to hold off for now.

     Mollymauk goes to tangle himself back into Caleb, after he had also taken his pants and short clothes off as well, situating themselves to have Molly startle Caleb's thigh a bit, so he could finger him easier and Molly had the bonus warm thigh to grind his dick into. Together they work Caleb's fingers into Molly's ass, starting with two now, stretching and thrusting them in deep, building up enough until Caleb can slip in another one. Molly is a mess as Caleb's nimble digits perfectly finger him, gentle but also full of intent and purpose. Hitting all the right nerves and sending shivers up Molly's spine. Making him pant against Caleb's shoulder, biting down particularly hard when on a certain deep thrust Caleb presses into Molly's prostate, unleashing a full deep moan. More than certain whoever was bunking next to them heard. Hopefully it wasn't Jester and Beau.

     Once Caleb add the third finger Mollymauk knows he's going to cum before they can go any further, every time the three finger slip into his ass it shoots pleasure through his body, now that he knew the magic spot every time Caleb made sure to press against it. On top of the fact that Molly couldn't help himself from grinding into Caleb's thigh, their cocks gliding against each other anytime Molly's hips bucked making both of them moan out loud. Eyes squeezed shut Molly doesn't even get the chance to warn Caleb other than a quick desperate whine of, "C-Caleb, I'm gonna-" before Molly's cock twitches and cum shoots out of it landing all over Caleb's thighs with a bit landing on his achingly hard dick, as he muffles the loud string of moans and screams into the freckle covered shoulder.

     Pulling his fingers out, Caleb watches Molly's chest heave with his heavy breathing, letting him recover before Caleb can deal with his own needs. He's got a bit of pride in himself, that he managed to make Mollymauk cum like that with just his fingers and not much more. "Molly, are you alright?" Caleb asks after a moment, concerned, but he knew Mollymauk would be alright. He was still covered in cum and would like very much to do that himself in some way. Mollymauk rolls onto his back running a hand through his thick purple hair, still catching his breath after that, his body practically spent now and he doesn't even want to know what his make up is like with how much he's sweating. "More than alright actually," He says probably much later than Caleb wanted an answer, but he's definitely not done yet. "C'mon, you going to finish what you started?" Molly breathes out, eyes bouncing from Caleb's flushed face, and the cock flared pink, decorated in Molly's fresh cum, looking more desperate than Molly did earlier.

     That was all Caleb needed to hear, before standing up on his knees and moving to kneel between Molly's spread open thighs. Using the lube like substance on his hand Caleb strokes his cock a few times, to make it a little easier on Mollymauk, his face going flush for a different reason now. "I'm actually really close too Molly, not really sure how long..." Caleb begins to trail off, looking embarrassed of all things right now, and Mollymauk is quick to shut him up. "I'm not worried about that Caleb. Besides you did better than me, I couldn't even wait for you to get your dick in my ass." Molly's thighs wrap around Caleb's waist, bringing him in closer, trying to encourage him to actually fuck him now.

     The same familiar burn of pressure comes back as Caleb eases his heavy cock into Molly's hole, everything was more sensitive now that he had cum already, the barely there nudge against his prostate already making his dick give another half hearted attempt. Bracing one hand on the bed and the other on Molly's hip, Caleb thrusts into the tight heat of Mollymauk's ass, testing his limits to see what felt good and what made Molly wince in pain. How hard he could thrust and building up a steady rhythm. Molly had already come and Caleb was close to begin with, he wasn't try to make this last as long as he could. Caleb wasn't sure how long he could normally anyways, Molly's body was hot and delicious feeling around his aching dick, every thrust seemingly better and than deeper than the last. Just barely feeling like Molly wasn't opened enough, but still hungrily taking it over and over again.

     Mollymauk isn't even half hard, but he was in pure ecstasy, he watched Caleb's flush face as he moaned and fucked Mollymauk senseless. Caleb's blue eyes flicker open meeting Molly's, he swallows hard and can tell Caleb is close. His chest was heaving, sweat running down into the matted chest hair, and his moans were getting louder and quicker with his heavy breath. The thrusts against Molly's hips more powerful, quick and desperate, and his grip tight making his knuckles white. "Where?" Caleb manages out between breaths, eyes not leaving Molly's. Mollymauk pauses trying to think of an answer, his brain still not fully working, because holy shit Caleb Widogast is fucking him. It doesn't matter what Mollymauk was going to say anyways, because he took to long to decide, as Caleb pulls out practically mid thrust, coming onto Mollymauk's waist, splashing up his stomach, covering his lilac skin with warm, thick, white ropes of cum. Caleb fucks his cock between Molly's dick and thigh, through the aftermath until he stops coming, and collapses down on the bed again next to Mollymauk.

     After a moment of no one saying a word, the room filled only with heavy panting and the smell of sweat and sex, Caleb reaches out to grab his short clothes from where he tossed them, giving Molly his thin undershirt. Mollymauk snatches it and wipes himself down, getting as much as the come off of him that he can, before tossing it to the floor again. Suddenly exhausted Molly turns to Caleb going to curl up with him, see that the latter made a half attempt at cleaning Molly's cum off himself, before tossing the rag and already fast asleep. Nuzzling against Caleb's back, he's out as well not even a moment later.

-

     Thinking back on the memory, Mollymauk shifts in his seat covering up his half hard on, "Easily one of the best nights of my life. If that means anything considering I've only been around for a few of them so far." Molly says, not giving Jester any of the graphic details, he knows the tiefling is hoping Molly would give to her freely. It would take a lot more alcohol that this to ever do that. "You guys aren't any fun." Jester says with a bit of a pout, obviously disappointed that they didn't share sex stories like they did where she was from. "Well, maybe once you get a significant other, you can tell us stories and we will tell you ours in return." Yasha finally says something about the situation, resting her empty bowl to the side and swinging an arm around Beau. Jester pinches her face up in thought, before eyeing Fjord very carefully again, before the innocent smile comes back to her features.

**Author's Note:**

> Also always use condoms kids


End file.
